Nitroalkanes are important intermediates in organic synthesis for the introduction of nitrogen atoms into organic molecules. A highly desirable route to incorporate nitro-groups into alkyl frameworks involves the alkylation of nitronate-anions using simple alkyl electrophiles. Despite the seeming simplicity of this disconnection, reaction conditions allowing for C-alkylation of the nitronate using readily available reagents has remained an open challenge in organic synthesis for more than seventy years.Recently we have discovered a simple solution to this long-standing problem in copper-based homogenous catalysts that allow for the high-yielding alkylation of nitronate-anions using simple, commercially available benzyl bromide electrophiles. These operationally simple reactions proceed under mild conditions and lead to high yields of complex nitroalkanes. Additionally, the current work provides facile access to phenethylamines, a common pharmacophore in many biologically active molecules. The scope and limitation of this method, as well as the future directions of this research program, will be discussed.

Copper-catalyzed <i>C</i>-benzylation of nitroalkanes

244th National Meeting (2012)

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Copper-catalyzed C-benzylation of nitroalkanes